Farnesene dimers and/or farnesane dimers and compositions thereof

ABSTRACT

Farnesene dimers and/or farnesane dimers and compositions thereof are described. The compositions provided comprise conventional additives. Methods of making and using the compounds and composition are also disclosed.

PRIOR RELATED APPLICATIONS

This application is a National stage of International Application No.PCT/US2009/005543, filed Oct. 9, 2009 which claims priority to U.S.Provisional Patent Application Nos. 61/104,675, filed Oct. 10, 2008 and61/244,406, filed Sep. 21, 2009, and U.S. application Ser. No.12/409,437, filed Mar. 23, 2009, the contents of which are incorporatedherein by reference in their entireties.

FIELD

Provided herein are farnesene dimers and/or farnesane dimers andcompositions comprising the same. Also provided are methods of makingand using the farnesene dimers and/or farnesane dimers. In certainembodiments, the farnesene dimers and/or farnesane dimers andcompositions thereof have use as lubricants, lubricity enhancers, pourpoint depressants or fuel additives.

BACKGROUND

Considerable effort has been expended to develop compositions for use inindustrial applications associated with the automotive, tractor,airline, railroad industries, metal-working industry and the like. Thereis a continuing demand for cost-effective compositions exhibitingimproved characteristics.

SUMMARY

In one embodiment, provided herein are compositions comprising farnesenedimers and/or farnesane dimers. In one embodiment, provided herein arecompositions comprising:

and one or more compounds selected from:

wherein, in each compound A, B, C or D, the dual lines consisting of asolid and a broken line represent single or double bonds such that eachgiven compound is either fully saturated or fully unsaturated. In otherwords, in a given compound A, B, C or D, when one dual line represents asingle bond then all dual lines in that compound represent single bonds.When one dual line in a given compound A, B, C or D represents a doublebond then all dual lines in that compound represent double bonds.

In one embodiment, compound A is

In one embodiment, compound A is

In one embodiment the one or more compounds are selected from:

In another embodiment, the compositions comprise two or more compoundsselected from I-A, I-B, I-C, and I-D.

In another embodiment, the compositions comprise two or more compoundsselected from II-A, II-B, II-C, and II-D.

In one embodiment, compositions provided herein comprise farnesenedimers of formulas I-A and I-B. In another embodiment, compositionscomprise farnesene dimers of formulas I-A, I-B, I-C and I-D. In anotherembodiment, compositions provided herein comprise farnesane dimers offormulas II-A, II-B, II-C and II-D. In one embodiment, compositionsprovided herein comprise farnesane dimers of formulas II-A and II-B. Inanother embodiment, compositions provided herein comprise farnesenedimers and/or farnesane dimers of formulas I-A, I-B, I-C, I-D, II-A,II-B, II-C, II-D or a mixture thereof.

In certain embodiments, provided herein is a compound selected from thegroup consisting of I-A, I-C, I-D, II-A, II-C, and II-D.

In certain embodiments, provided herein is a composition comprisingcompounds I-A and I-B. In certain embodiments, the composition furthercomprises compounds I-C and I-D. In certain embodiments, provided hereinis a composition comprising compounds II-A and II-B. In certainembodiments, the composition further comprises compounds II-C and II-D.

In certain embodiments, said compositions are lubricant compositions. Inone embodiment, the lubricant compositions provided herein comprisefarnesene dimers of formulas I-A and I-B. In another embodiment, thelubricant compositions comprise farnesene dimers of formulas I-A, I-B,I-C and I-D. In another embodiment, the lubricant compositions comprisefarnesane dimers of formulas II-A, II-B, II-C and II-D. In oneembodiment, the lubricant compositions provided herein comprisefarnesane dimers of formulas II-A and II-B. In another embodiment, thelubricant compositions comprise farnesene dimers and/or farnesane dimersof formulas I-A, I-B, I-C, I-D, II-A, II-B, II-C and II-D.

In certain embodiments, provided herein are compositions comprisingfarnesane dimer II-A and a compound selected from squalane, squalene,and(6E,11E,18E)-2,6,19,23-tetramethyl-10,15-dimethylenetetracosa-2,6,11,18,22-pentaene.In one embodiment, the compositions further comprise farnesane dimerII-B. In another embodiment, the compositions further comprise acompound selected from I-A, I-B, I-C, I-D, II-C and II-D.

In one embodiment, a composition provided herein comprises farnesanedimer II-A or farnesane dimer II-B, and a compound selected fromsqualane, squalene, and(6E,11E,18E)-2,6,19,23-tetramethyl-10,15-dimethylenetetracosa-2,6,11,18,22-pentaene.In one embodiment, a composition provided herein comprises farnesanedimer II-A or farnesane dimer II-B, and squalane. In another embodiment,a composition provided herein comprises I-A, I-B, I-C, I-D, II-A, II-B,II-C or II-D and a compound selected from squalane, squalene, and(6E,11E,18E)-2,6,19,23-tetramethyl-10,15-dimethylenetetracosa-2,6,11,18,22-pentaene.In one embodiment, a composition provided herein comprises farnesanedimer II-A and squalane.

In certain embodiments, compositions provided herein have a viscosityindex greater than about 200 according to ASTM D 2270. In certainembodiments, the viscosity index is from about 230 to about 240according to ASTM D 2270. The compositions provided herein can exist asliquid compositions at room temperature.

In certain embodiments, compositions provided herein have a viscosityindex of about 80 or greater according to ASTM D 2270. In certainembodiments, the viscosity index is from about 90 to about 150 accordingto ASTM D 2270.

In certain embodiments, the farnesene dimers and/or farnesane dimers andcompositions thereof have utility as lubricity enhancers, pour pointdepressants and/or fuel additives. The farnesene dimers and/or farnesanedimers and compositions thereof can be used in a wide variety ofapplications, including but not limited to, applications associated withthe automotive, tractor, airline, and railroad industries includingengines, transmissions, and the like, metal-working fluids, quenchfluids, greases, crankcase lubricants, power transmission fluids,vehicle axle applications, hydraulic systems, heavy duty gear oils, androtating machinery such as stationary engines, pumps, gas turbines,compressors, wind turbines, and the like. Stationary engines includefuel and gas powered engines that are not associated with theautomotive, tractor, airline, and railroad industries. Also provided aremethods of making the compounds and compositions.

In certain embodiments, compositions provided herein are readilybiodegradable. In certain embodiments, compositions provided herein arelow in toxicity and pose little or no harm to aquatic organisms orsurrounding vegetation. These qualities are particularly useful forapplications in environmentally sensitive areas such as marineecosystems, and for those with a high potential of being lost to thesurrounding environment. In certain embodiments, compositions providedherein can be derived from readily available, renewable materials.

In certain embodiments, provided herein is a method of lubricating amachine by operating the machine in contact with a composition providedherein. The compositions can be used for lubricating any machine thatneeds lubrication. Exemplary machines include, but are not limited toengines, pumps, gas turbines, compressors, wind turbines, and the like.In certain embodiments, the engine is a fuel and/or gas powered engineassociated with the automotive, tractor, airline, and railroadindustries. In certain embodiments, the engine is a stationary engine,including a fuel and/or gas powered engine that is not associated withthe automotive, tractor, airline, and railroad industries.

In certain embodiments, provided herein is a machine comprising acomposition provided herein.

DESCRIPTION OF THE DRAWINGS

FIG. 1 shows the relationship of kinetic viscosity for various blends ofsqualane and farnesane dimer II-A at 40 and 100° C.

FIG. 2 shows viscosity index for various blends of squalane andfarnesane dimer II-A.

DEFINITIONS

In the following description, all numbers disclosed herein areapproximate values, regardless whether the word “about” or “approximate”is used in connection therewith. Numbers may vary by 1 percent, 2percent, 5 percent, or, sometimes, 10 to 20 percent. Whenever anumerical range with a lower limit, R^(L), and an upper limit, R^(U), isdisclosed, any number falling within the range is specificallydisclosed. In particular, the following numbers within the range arespecifically disclosed: R=R^(L)+k*(R^(U)−R^(L)), wherein k is a variableranging from 1 percent to 100 percent with a 1 percent increment, i.e.,k is 1 percent, 2 percent, 3 percent, 4 percent, 5 percent, . . . , 50percent, 51 percent, 52 percent, . . . , 95 percent, 96 percent, 97percent, 98 percent, 99 percent, or 100 percent. Moreover, any numericalrange defined by two R numbers as defined in the above is alsospecifically disclosed.

As used herein, “β-Farnesene” refers to a compound having the followingformula:

or a stereoisomer thereof. In some embodiments, the β-farnesenecomprises a substantially pure stereoisomer of β-farnesene. In otherembodiments, the β-farnesene comprises a mixture of stereoisomers, suchas cis-trans isomers. In further embodiments, the amount of each of thestereoisomers in the β-farnesene mixture is independently from about 0.1wt. % to about 99.9 wt. %, from about 0.5 wt. % to about 99.5 wt. %,from about 1 wt. % to about 99 wt. %, from about 5 wt. % to about 95 wt.%, from about 10 wt. % to about 90 wt. %, from about 20 wt. % to about80 wt. %, based on the total weight of the β-farnesene mixture.

As used herein, “squalane” refers to a compound having the followingformula:

As used herein, “squalene” refers to a compound having the followingformula:

As used herein, “dehydrosqualene” or“(6E,11E,18E)-2,6,19,23-tetramethyl-10,15-dimethylenetetracosa-2,6,11,18,22-pentaene”refers to a compound having the following formula:

DESCRIPTION OF EMBODIMENTS

In one embodiment, provided herein are compositions comprising two ormore farnesene dimers and/or farnesane dimers.

In one embodiment, provided herein are compositions comprising:

and one or more compounds selected from:

such that in a given compound A, B, C or D, when one dual linerepresents a single bond then all dual lines in that compound representsingle bonds. When one dual line in a given compound A, B, C or Drepresents a double bond then all dual lines in that compound representdouble bonds. In other words, in each compound A, B, C or D the duallines consisting of a solid and a broken line represent a single or adouble bonds such that each given compound is either fully saturated orfully unsaturated.

In one embodiment, compound A is

In one embodiment, compound A is

In one embodiment, the one or more compounds are selected from:

In another embodiment, the compositions comprise two or more compoundsselected from I-A, I-B, I-C and I-D.

In another embodiment, the compositions comprise two or more compoundsselected from II-A, II-B, II-C and II-D.

In one embodiment, compositions provided herein comprise farnesenedimers of formulas I-A and I-B. In another embodiment, compositionsprovided herein comprise farnesene dimers of formulas I-A, I-B, I-C andI-D.

In another embodiment, compositions provided herein comprise farnesanedimers of formulas II-A, II-B, II-C and II-D. In one embodiment,compositions provided herein comprise farnesane dimers of formulas II-Aand II-B. In another embodiment, compositions provided herein comprisefarnesene dimers and/or farnesane dimers of formulas I-A, I-B, I-C, I-D,II-A, II-B, II-C and II-D.

In certain embodiments, the amount of one or more farnesene dimersand/or farnesane dimers in compositions provided herein is at leastabout 0.1% based on the total weight of the composition. In certainembodiments, the amount of one or more farnesene dimers and/or farnesanedimers in compositions provided herein is from about 1 to about 95%based on the total weight of the composition. In certain embodiments,the amount of one or more farnesene dimers and/or farnesane dimers incompositions provided herein is at least about 0.1, 1, 2, 3, 4, 5, 7, 9,10, 15, 20, 25, 30, 35, 40, 45, 50, 60, 70, 80, 90, 92, 95, 96, 97, 98,99 or 99.5% based on the total weight of the composition.

In certain embodiments, the amount of farnesene dimer of formula I-A incompositions provided herein is at least about 10% based on the totalweight of the farnesene dimers. In certain embodiments, the amount offarnesene dimer of formula I-A in compositions provided herein is atleast about 20% based on the total weight of the farnesene dimers. Incertain embodiments, the amount of farnesene dimer of formula I-A incompositions provided herein is from about 25 to about 90%, about 25 toabout 80%, about 30 to about 70%, about 30 to about 60%, about 30 toabout 50% or about 30 to about 40% based on the total weight of thefarnesene dimers in the composition. In certain embodiments, the amountof farnesene dimer of formula I-A in the compositions is at least about5, 10, 12, 14, 15, 17, 20, 25, 30, 35, 37, 40, 50, 60, 70, 75, 80 or 90%based on the total weight of the farnesene dimers in the composition. Incertain embodiments, the amount of farnesene dimer of formula I-A in thecompositions is at least about 25, 30, 35, 40, 50, 60, 70, 75, 80 or 90%based on the total weight of the farnesene dimers in the composition.

In certain embodiments, the amount of farnesene dimer of formula I-B incompositions provided herein is at least about 10% based on the totalweight of the farnesene dimers. In certain embodiments, the amount offarnesene dimer of formula I-B in compositions provided herein is atleast about 20% based on the total weight of the farnesene dimers in thecomposition. In certain embodiments, the amount of farnesene dimer offormula I-B in compositions provided herein is at least about 25% basedon the total weight of the farnesene dimers in the composition. Incertain embodiments, the amount of farnesene dimer of formula I-B incompositions provided herein is from about 25 to about 90%, about 25 toabout 80%, about 30 to about 70%, about 30 to about 60%, about 30 toabout 50% or about 30 to about 40% based on the total weight of thefarnesene dimers in the composition. In certain embodiments, the amountof farnesene dimer of formula I-B in the compositions is at least about5, 10, 12, 14, 15, 17, 20, 25, 30, 35, 37, 40, 50, 60, 70, 75, 80 or 90%based on the total weight of the farnesene dimers in the composition. Incertain embodiments, the amount of farnesene dimer of formula I-B incompositions provided herein is at least about 25, 30, 35, 40, 50, 60,70, 75, 80 or 90% based on the total weight of the farnesene dimers inthe composition.

In certain embodiments, the amount of farnesene dimer of formula I-C incompositions provided herein is at least about 1% or about 2% based onthe total weight of the farnesene dimers in the composition. In certainembodiments, the amount of farnesene dimer of formula I-C incompositions provided herein is at least about 5% based on the totalweight of the farnesene dimers in the composition. In certainembodiments, the amount of farnesene dimer of formula I-C incompositions provided herein is from about 5 to about 40%, about 5 toabout 30%, about 10 to about 25% or about 10 to about 20% based on thetotal weight of the farnesene dimers in the composition. In certainembodiments, the amount of farnesene dimer of formula I-C incompositions provided herein is at least about 1, 2, 3, 4, 5, 6, 7, 8,9, 10, 11, 12, 15, 20, 25, 30, 35 or 40% based on the total weight ofthe farnesene dimers in the composition. In certain embodiments, theamount of farnesene dimer of formula I-C in compositions provided hereinis at least about 5, 10, 12, 15, 20, 25, 30, 35 or 40% based on thetotal weight of the farnesene dimers in the composition.

In certain embodiments, the amount of farnesene dimer of formula I-D incompositions provided herein is at least about 1% or about 2% based onthe total weight of the farnesene dimers in the composition. In certainembodiments, the amount of farnesene dimer of formula I-D incompositions provided herein is at least about 5% based on the totalweight of the farnesene dimers in the composition. In certainembodiments, the amount of farnesene dimer of formula I-D incompositions provided herein is from about 5 to about 40%, about 5 toabout 30%, about 10 to about 25% or about 10 to about 20% based on thetotal weight of the farnesene dimers in the composition. In certainembodiments, the amount of farnesene dimer of formula I-D incompositions provided herein is at least about 1, 2, 3, 4, 5, 6, 7, 8,9, 10, 11, 12, 15, 20, 25, 30, 35 or 40% based on the total weight ofthe farnesene dimers in the composition. In certain embodiments, theamount of farnesene dimer of formula I-D in compositions provided hereinis at least about 5, 10, 12, 15, 20, 25, 30, 35 or 40% based on thetotal weight of the farnesene dimers in the composition.

In certain embodiments, the total amount of farnesene dimers of formulasI-A and I-B in compositions provided herein is at least about 10% basedon the total weight of the farnesene dimers in the composition. Incertain embodiments, the total amount of farnesene dimers of formulasI-A and I-B in compositions provided herein is at least about 20% basedon the total weight of the farnesene dimers in the composition. Incertain embodiments, the total amount of farnesene dimers of formulasI-A and I-B in compositions provided herein is at least about 40% basedon the total weight of the farnesene dimers in the composition. Incertain embodiments, the total amount of farnesene dimers of formulasI-A and I-B in compositions provided herein is from about 40 to about90%, about 50 to about 85%, about 50 to about 80% or about 60 to about80% based on the total weight of the farnesene dimers in thecomposition. In certain embodiments, the total amount of farnesenedimers of formulas I-A and I-B in compositions provided herein is atleast about 5, 10, 15, 20, 25, 30, 35, 37, 40, 45, 50, 60, 70, 75, 80 or90% based on the total weight of the farnesene dimers in thecomposition. In certain embodiments, the total amount of farnesenedimers of formulas I-A and I-C in compositions provided herein is atleast about 40, 50, 60, 70, 75, 80 or 90% based on the total weight ofthe farnesene dimers in the composition.

In certain embodiments, the total amount of farnesene dimers of formulasI-C and I-D in compositions provided herein is at least about 1%, 2%,3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11% or 12% based on the total weight ofthe farnesene dimers in the composition. In certain embodiments, thetotal amount of farnesene dimers of formulas I-C and I-D in compositionsprovided herein is at least about 10% based on the total weight of thefarnesene dimers in the composition. In certain embodiments, the totalamount of farnesene dimers of formulas I-C and I-D in compositionsprovided herein is from about 10 to about 40%, about 10 to about 30%,about 10 to about 25% or about 10 to about 20% based on the total weightof the farnesene dimers in the composition. In certain embodiments, thetotal amount of farnesene dimers of formulas I-C and I-D in compositionsprovided herein is at least about 10, 15, 20, 25, 30, 35 or 40% based onthe total weight of the farnesene dimers in the composition.

In certain embodiments, the amount of farnesane dimer of formula II-A incompositions provided herein is at least about 10% based on the totalweight of the farnesane dimers in the composition. In certainembodiments, the amount of farnesane dimer of formula II-A incompositions provided herein is at least about 20% based on the totalweight of the farnesane dimers in the composition. In certainembodiments, the amount of farnesane dimer of formula II-A incompositions provided herein is at least about 25% based on the totalweight of the farnesane dimers in the composition. In certainembodiments, the amount of farnesane dimer of formula II-A incompositions provided herein is from about 25 to about 90%, about 25 toabout 80%, about 30 to about 70%, about 30 to about 60%, about 30 toabout 50% or about 30 to about 40% based on the total weight of thefarnesane dimers in the composition. In certain embodiments, the amountof farnesene dimer of formula II-A in the compositions is at least about5, 10, 12, 14, 15, 17, 20, 25, 30, 35, 37, 40, 45, 50, 60, 70, 75, 80 or90% based on the total weight of the farnesene dimers in thecomposition. In certain embodiments, the amount of farnesane dimer offormula II-A in compositions provided herein is at least about 25, 30,35, 40, 50, 60, 70, 75, 80 or 90% based on the total weight of thefarnesane dimers in the composition.

In certain embodiments, the amount of farnesane dimer of formula II-B incompositions provided herein is at least about 20% based on the totalweight of the farnesane dimers in the composition. In certainembodiments, the amount of farnesane dimer of formula II-B incompositions provided herein is at least about 25% based on the totalweight of the farnesane dimers in the composition. In certainembodiments, the amount of farnesane dimer of formula II-B incompositions provided herein is from about 25 to about 90%, about 25 toabout 80%, about 30 to about 70%, about 30 to about 60%, about 30 toabout 50% or about 30 to about 40% based on the total weight of thefarnesane dimers in the composition. In certain embodiments, the amountof farnesene dimer of formula II-B in the compositions is at least about10, 12, 14, 15, 17, 20, 25, 30, 35, 37, 40, 45, 50, 60, 70, 75, 80 or90% based on the total weight of the farnesene dimers in thecomposition. In certain embodiments, the amount of farnesane dimer offormula II-B in compositions provided herein is at least about 25, 30,35, 40, 50, 60, 70, 75, 80 or 90% based on the total weight of thefarnesane dimers in the composition.

In certain embodiments, the amount of farnesane dimer of formula II-C incompositions provided herein is at least about 5% based on the totalweight of the farnesane dimers in the composition. In certainembodiments, the amount of farnesane dimer of formula II-C incompositions provided herein is from about 5 to about 40%, about 5 toabout 30%, about 10 to about 25% or about 10 to about 20% based on thetotal weight of the farnesane dimers in the composition. In certainembodiments, the amount of farnesene dimer of formula II-C incompositions provided herein is at least about 1, 2, 3, 4, 5, 6, 7, 8,9, 10, 11, 12, 15, 20, 25, 30, 35 or 40% based on the total weight ofthe farnesene dimers in the composition. In certain embodiments, theamount of farnesane dimer of formula II-C in compositions providedherein is at least about 5, 10, 12, 15, 20, 25, 30, 35 or 40% based onthe total weight of the farnesane dimers in the composition.

In certain embodiments, the amount of farnesane dimer of formula II-D incompositions provided herein is at least about 5% based on the totalweight of the farnesane dimers in the composition. In certainembodiments, the amount of farnesane dimer of formula II-D incompositions provided herein is from about 5 to about 40%, about 5 toabout 30%, about 10 to about 25% or about 10 to about 20% based on thetotal weight of the farnesane dimers in the composition. In certainembodiments, the amount of farnesene dimer of formula II-D incompositions provided herein is at least about 1, 2, 3, 4, 5, 6, 7, 8,9, 10, 11, 12, 15, 20, 25, 30, 35 or 40% based on the total weight ofthe farnesene dimers in the composition. In certain embodiments, theamount of farnesane dimer of formula II-D in compositions providedherein is at least about 5, 10, 12, 15, 20, 25, 30, 35 or 40% based onthe total weight of the farnesane dimers in the composition.

In certain embodiments, the total amount of farnesane dimers of formulaII-A and II-B in compositions provided herein is at least about 40%based on the total weight of the farnesane dimers in the composition. Incertain embodiments, the total amount of farnesane dimers of formulasII-A and II-B in compositions provided herein is from about 40 to about99.5%, about 50 to about 90%, about 50 to about 85% or about 60 to about80% based on the total weight of the farnesane dimers in thecomposition. In certain embodiments, the total amount of farnesenedimers of formulas II-A and II-B in compositions provided herein is atleast about 10, 15, 20, 25, 30, 35, 37, 40, 45, 50, 60, 70, 75, 80 or90% based on the total weight of the farnesene dimers in thecomposition. In certain embodiments, the total amount of farnesanedimers of formulas II-A and II-B in compositions provided herein is atleast about 40, 50, 60, 70, 75, 80 or 90% based on the total weight ofthe farnesane dimers in the composition.

In certain embodiments, the total amount of farnesene dimers of formulasII-C and II-D in compositions provided herein is at least about 1%, 2%,3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11% or 12% based on the total weight ofthe farnesene dimers in the composition. In certain embodiments, thetotal amount of farnesane dimers of formulas II-C and II-D incompositions provided herein is at least about 10% based on the totalweight of the farnesane dimers in the composition. In certainembodiments, the total amount of farnesane dimers of formula II-C andII-D in compositions provided herein is from about 10 to about 40%,about 10 to about 30%, about 10 to about 25% or about 10 to about 20%based on the total weight of the farnesane dimers in the composition. Incertain embodiments, the total amount of farnesane dimers of formulaII-C and II-D in compositions provided herein is at least about 10, 15,20, 25, 30, 35 or 40% based on the total weight of the farnesane dimersin the composition.

In certain embodiments, compositions provided herein comprise farnesenedimers of formulas I-A, I-B, I-C and I-D. In one embodiment, the amountof farnesene dimer of formula I-A in compositions provided herein is atleast about 10%, the amount of farnesene dimer of formula I-B incompositions provided herein is at least about 10%, the amount offarnesene dimer of formula I-C in compositions provided herein is atleast about 1% and the amount of farnesene dimer of formula I-D incompositions provided herein is at least about 1% based on the totalweight of the farnesene dimers in the composition. In one embodiment,the amount of farnesene dimer of formula I-A in compositions providedherein is at least about 20%, the amount of farnesene dimer of formulaI-B in compositions provided herein is at least about 20%, the amount offarnesene dimer of formula I-C in compositions provided herein is atleast about 2% and the amount of farnesene dimer of formula I-D incompositions provided herein is at least about 2% based on the totalweight of the farnesene dimers in the composition. In one embodiment,the amount of farnesene dimer of formula I-A in compositions providedherein is at least about 30%, the amount of farnesene dimer of formulaI-B in compositions provided herein is at least about 30%, the amount offarnesene dimer of formula I-C in compositions provided herein is atleast about 5% and the amount of farnesene dimer of formula I-D incompositions provided herein is at least about 5% based on the totalweight of the farnesene dimers in the composition. In one embodiment,the amount of farnesene dimer of formula I-A in compositions providedherein is from about 30% to about 50%, the amount of farnesene dimer offormula I-B in compositions provided herein is from about 30% to about50%, the amount of farnesene dimer of formula I-C in compositionsprovided herein is from about 5% to about 15% and the amount offarnesene dimer of formula I-D in compositions provided herein is fromabout 5% to about 15% based on the total weight of the farnesene dimersin the composition. In one embodiment, compositions provided hereincomprise farnesene dimer of formula I-A in about 40%, farnesene dimer offormula I-B in about 40%, farnesene dimer of formula I-C in about 10%,and farnesene dimer of formula I-D in about 10% based on the totalweight of the farnesene dimers in the composition.

In certain embodiments, the compositions provided herein comprisefarnesane dimers of formula II-A, II-B, II-C and II-D. In oneembodiment, the amount of farnesane dimer of formula II-A incompositions provided herein is at least about 10%, the amount offarnesane dimer of formula II-B in compositions provided herein is atleast about 10%, the amount of farnesane dimer of formula II-C incompositions provided herein is at least about 1% and the amount offarnesane dimer of formula II-D in compositions provided herein is atleast about 1% based on the total weight of the farnesane dimers in thecomposition. In one embodiment, the amount of farnesane dimer of formulaII-A in compositions provided herein is at least about 20%, the amountof farnesane dimer of formula II-B in compositions provided herein is atleast about 20%, the amount of farnesane dimer of formula II-C incompositions provided herein is at least about 2% and the amount offarnesane dimer of formula II-D in compositions provided herein is atleast about 2% based on the total weight of the farnesane dimers in thecomposition. In one embodiment, the amount of farnesane dimer of formulaII-A in compositions provided herein is at least about 30%, the amountof farnesane dimer of formula II-B in compositions provided herein is atleast about 30%, the amount of farnesane dimer of formula II-C incompositions provided herein is at least about 5% and the amount offarnesane dimer of formula II-D in compositions provided herein is atleast about 5% based on the total weight of the farnesane dimers in thecomposition. In one embodiment, the amount of farnesane dimer of formulaII-A in compositions provided herein is from about 30% to about 50%, theamount of farnesane dimer of formula II-B in compositions providedherein is from about 30% to about 50%, the amount of farnesane dimer offormula II-C in compositions provided herein is from about 5% to about15% and the amount of farnesane dimer of formula II-D in compositionsprovided herein is from about 5% to about 15% based on the total weightof the farnesane dimers in the composition. In one embodiment,compositions provided herein comprise farnesane dimer of formula II-A inabout 40%, farnesane dimer of formula II-B in about 40%, farnesane dimerof formula II-C in about 10%, and farnesane dimer of formula II-D inabout 10% based on the total weight of the farnesane dimers in thecomposition.

In certain embodiments, compositions provided herein comprise farnesenedimers of formula I-A:I-B:I-C:I-D in a ratio of 4:4:1:1. In certainembodiments, compositions provided herein comprise farnesane dimers offormula II-A:II-B:II-C:II-D in a ratio of 4:4:1:1.

In one embodiment, provided herein are compositions comprising farnesanedimer II-A and a compound selected from squalane, squalene, and(6E,11E,18E)-2,6,19,23-tetramethyl-10,15-dimethylenetetracosa-2,6,11,18,22-pentaene.In one embodiment, the compositions further comprise farnesane dimerII-B. In another embodiment, the compositions further comprise afarnesane dimer selected from II-C, and II-D. In another embodiment, thecompositions further comprise a farnesane dimer selected from I-A, I-B,I-C, and I-D.

In one embodiment, a composition provided herein comprises farnesanedimer II-A or farnesane dimer II-B, and a compound selected fromsqualane, squalene, and(6E,11E,18E)-2,6,19,23-tetramethyl-10,15-dimethylenetetracosa-2,6,11,18,22-pentaene.

In another embodiment, a composition provided herein comprises farnesenedimer and/or farnesane dimer I-A, I-B, I-C, I-D, II-A, II-B, II-C orII-D, and a compound selected from squalane, squalene, and(6E,11E,18E)-2,6,19,23-tetramethyl-10,15-dimethylenetetracosa-2,6,11,18,22-pentaene.

In one embodiment, provided herein is a composition comprising farnesanedimer II-A, and squalane. In one embodiment, the composition furthercomprises farnesane dimer II-B. In one embodiment, the compositionfurther comprises I-A, I-B, I-C, I-D, II-C, II-D or a mixture thereof.

In certain embodiments, the amount of farnesane dimer II-A incompositions provided herein is about 1% or greater based on the totalweight of the composition. In certain embodiments, the amount offarnesane dimer II-A in compositions provided herein is from about 1 toabout 95% based on the total weight of the composition. In certainembodiments, the amount of farnesane dimer II-A in compositions providedherein is about 1, 3, 5, 7, 10, 12, 15, 17, 20, 23, 25, 27, 30, 33, 35,37, 40, 43, 45, 47, 50, 60, 70, 80, 90, or 95% or greater based on thetotal weight of the composition.

In certain embodiments, the amount of farnesane dimer II-B incompositions provided herein about 1% or greater based on the totalweight of the composition. In certain embodiments, the amount offarnesane dimer II-A in compositions provided herein is from about 1 toabout 80% based on the total weight of the composition. In certainembodiments, the amount of farnesane dimer II-A in compositions providedherein is about 1, 3, 5, 7, 10, 12, 15, 17, 20, 23, 25, 27, 30, 33, 35,37, 40, 43, 45, 47, 50, 60, 70, or 80% or greater based on the totalweight of the composition.

In certain embodiments, the total amount of farnesene dimers and/orfarnesane dimers I-A, I-B, I-C, I-D, II-C and II-D in compositionsprovided herein is about 0.1% or greater based on the total weight ofthe composition. In certain embodiments, the total amount of farnesenedimers and/or farnesane dimers I-A, I-B, I-C, I-D, II-C and II-D incompositions provided herein is about 1% or greater based on the totalweight of the composition. In certain embodiments, the total amount offarnesene dimers and/or farnesane dimers I-A, I-B, I-C, I-D, II-C andII-D in compositions provided herein is about 1 to 20% or greater basedon the total weight of the farnesene dimers. In certain embodiments, thetotal amount of farnesene dimers and/or farnesane dimers I-A, I-B, I-C,I-D, II-C and II-D in compositions provided herein is about 0.1, 1, 2,3, 4, 5, 6, 10, 12, 15, 17, 20, 25, 30, 35, 40 or 50% or greater basedon the total weight of the farnesene dimers.

In certain embodiments, the total amount of squalane, squalene anddehydrosqualene in compositions provided herein is about 1% or greaterbased on the total weight of the composition. In certain embodiments,the total amount of squalane, squalene and dehydrosqualene incompositions provided herein is from about 5 to about 90% based orgreater on the total weight of the composition. In certain embodiments,the total amount of squalane, squalene and dehydrosqualene incompositions provided herein is about 1, 3, 5, 7, 10, 12, 15, 17, 20,23, 25, 27, 30, 33, 35, 37, 40, 43, 45, 47, 50, 60, 70, 80 or 90% orgreater based on the total weight of the composition.

In certain embodiments, the amount of squalane in compositions providedherein is about 1% or greater based on the total weight of thecomposition. In certain embodiments, the total amount of squalane incompositions provided herein is from about 1 to about 95% or 5 to about90% or greater based on the total weight of the composition. In certainembodiments, the total amount of squalane in compositions providedherein is about 1, 3, 5, 7, 10, 12, 15, 17, 20, 23, 25, 27, 30, 33, 35,37, 40, 43, 45, 47, 50, 60, 70, 80, or 90% or greater based on the totalweight of the composition.

In certain embodiments, the amount of squalene in compositions providedherein is about 1% or greater based on the total weight of thecomposition. In certain embodiments, the total amount of squalene incompositions provided herein is from about 1 to about 90%, about 1 toabout 50%, about 1 to about 30% or greater based on the total weight ofthe composition. In certain embodiments, the total amount of squalene incompositions provided herein is about 1, 3, 5, 7, 10, 12, 15, 17, 20,23, 25, 27, 30, 33, 35, 37, 40, 43, 45, 47, 50, 60, 70, 80 or 90% orgreater based on the total weight of the composition.

In certain embodiments, the amount of dehydrosqualene in compositionsprovided herein is about 1% or greater based on the total weight of thecomposition. In certain embodiments, the total amount of dehydrosqualenein compositions provided herein is from about 1 to about 90%, about 1 toabout 50%, about 1 to about 30% or greater based on the total weight ofthe composition. In certain embodiments, the total amount ofdehydrosqualene in compositions provided herein is about 1, 3, 5, 7, 10,12, 15, 17, 20, 23, 25, 27, 30, 33, 35, 37, 40, 43, 45, 47, 50, 60, 70,80 or 90% or greater based on the total weight of the composition.

In certain embodiments, the compounds and compositions provided hereinhave viscosity at 100° C. from about 5 centistokes (cSt) to about 20cSt, from about 5 centistokes (cSt) to about 15 cSt, or from about 7 cStto about 13 cSt. In certain embodiments, the compounds and compositionshave viscosity of about 10 cSt at 100° C. In certain embodiments, thecompounds and compositions provided herein have viscosity at 40° C. fromabout 25 centistokes (cSt) to about 50 cSt, from about 30 centistokes(cSt) to about 50 cSt, or from about 35 cSt to about 45 cSt. In certainembodiments, the compounds and compositions have viscosity of about 43cSt at 40° C. The viscosity of the compounds and compositions disclosedherein can be measured according to ASTM D 445.

In certain embodiments, the compounds and compositions provided hereinhave a viscosity index greater than about 200 according to ASTM D 2270.In certain embodiments, the viscosity index is greater than about 220according to ASTM D 2270. In certain embodiments, the viscosity index isfrom about 220 to about 245 according to ASTM D 2270. In certainembodiments, the viscosity index is from about 230 to about 240according to ASTM D 2270.

In certain embodiments, the compositions provided herein have kineticviscosity of about 3 centistokes (cSt) or greater at 100° C. In certainembodiments, the compositions provided herein have kinetic viscosity ofabout 4 centistokes (cSt) or greater at 100° C. In certain embodiments,the compositions provided herein have kinetic viscosity from about 3 cStto about 10 cSt, from about 4 cSt to about 8 cSt, or from about 4 cSt toabout 6 cSt at 100° C. In certain embodiments, the compositions providedherein have kinetic viscosity from about 3 centistokes (cSt) to about 10cSt, from about 4 cSt to about 8 cSt, or from about 4 cSt to about 6 cStat 100° C. In certain embodiments, the compositions provided herein havekinetic viscosity of about 4, 5, or 6 cSt at 100° C.

In certain embodiments, the compositions provided herein have kineticviscosity of about 15 cSt or greater at 40° C. In certain embodiments,the compositions provided herein have kinetic viscosity of about 20 cStor greater at 40° C. In certain embodiments, the compositions providedherein have kinetic viscosity from about 15 cSt to about 40 cSt, fromabout 20 cSt to about 40 cSt, or from about 20 cSt to about 30 cSt at40° C. In certain embodiments, the compositions have kinetic viscosityof about 20, 25, 30 or 35 cSt at 40° C. The kinetic viscosity of thecompositions disclosed herein can be measured according to ASTM D 445.

In certain embodiments, the compositions provided herein have dynamicviscosity of about 10 cP or greater at 40° C. In certain embodiments,the compositions provided herein have dynamic viscosity of about 15 cPor greater at 40° C. In certain embodiments, the compositions providedherein have dynamic viscosity from about 10 cP to about 40 cP, fromabout 15 cP to about 30 cP, or from about 15 cP to about 25 cP at 40° C.In certain embodiments, the compositions provided herein have dynamicviscosity of about 15, 17, 20, 22, or 25 cP at 40° C.

In certain embodiments, the compositions provided herein have dynamicviscosity of about 2 cP or greater at 100° C. In certain embodiments,the compositions provided herein have dynamic viscosity of about 3 cP orgreater at 100° C. In certain embodiments, the compositions providedherein have dynamic viscosity from about 1 cP to about 10 cP, from about1 cP to about 7 cP, or from about 2 cP to about 5 cP at 100° C. Incertain embodiments, the compositions have dynamic viscosity of about 2,3, 4 or 5 cP at 100° C. The dynamic viscosity of the compositionsdisclosed herein can be measured according to ASTM D 445.

In certain embodiments, compositions provided herein have a viscosityindex about 90 or greater according to ASTM D 2270. In certainembodiments, compositions provided herein have a viscosity index about100 or greater according to ASTM D 2270. In certain embodiments, theviscosity index is from about 90 to about 140 or about 100 to about 130according to ASTM D 2270. In certain embodiments, the viscosity index isfrom about 110 to about 130 according to ASTM D 2270. In certainembodiments, the viscosity index is about 100, 110, 120, 125 or about130 according to ASTM D 2270.

In certain embodiments, the compositions provided herein have density ofabout 0.700 to about 0.900 at 40° C. In certain embodiments, thecompositions provided herein have density of about 0.700 to about 0.850at 40° C. In certain embodiments, the compositions provided herein havedensity of about 0.700. 0.750, 0.800, 0.850 or 0.900 at 40° C. Incertain embodiments, the compositions provided herein have density ofabout 0.700 to about 0.800 at 100° C. In certain embodiments, thecompositions provided herein have density of about 0.700. 0.750, or0.800 at 100° C.

In certain embodiments, the compounds and compositions provided hereinhave use as lubricity enhancers. In another embodiment, provided hereinare lubricity enhancer compositions comprising one or more compounds offormula I-A, I-B, I-C, I-D, II-A, II-B, II-C, and II-D and a suitablelubricating oil additive. In certain embodiments, the lubricity enhancercompositions comprise between 0.1 and 75%, between 1 and 65%, or between5 and 50% of the compound of formula I-A, I-B, I-C, I-D, II-A, II-B,II-C, II-D or a combination thereof.

In one embodiment, a composition provided herein comprises farnesanedimer II-A or farnesane dimer II-B; a compound selected from squalane,squalene, and(6E,11E,18E)-2,6,19,23-tetramethyl-10,15-dimethylenetetracosa-2,6,11,18,22-pentaene;and a suitable lubricating oil additive.

Any lubricating oil additive known to a person of ordinary skill in theart may be used in the lubricity enhancer compositions disclosed herein.In some embodiments, the lubricating oil additive can be selected fromthe group consisting of antioxidants, antiwear agents, detergents, rustinhibitors, demulsifiers, friction modifiers, multi-functionaladditives, pour point depressants, foam inhibitors, metal deactivators,dispersants, corrosion inhibitors, thermal stability improvers, dyes,markers, and combinations thereof.

In another embodiment, provided herein are lubricity enhancercompositions comprising a compound of formula I-A, I-B, I-C, I-D, II-A,II-B, II-C, II-D or a combination thereof, a suitable additive andoptionally a base oil of lubricating viscosity.

In one embodiment, a composition provided herein comprises farnesanedimer II-A or farnesane dimer II-B; a compound selected from squalane,squalene, and(6E,11E,18E)-2,6,19,23-tetramethyl-10,15-dimethylenetetracosa-2,6,11,18,22-pentaene;a suitable additive and optionally a base oil of lubricating viscosity.

Any base oil known to a skilled artisan can be used as the oil oflubricating viscosity disclosed herein. Some base oils suitable forpreparing the lubricant compositions have been described in Mortier etal., “Chemistry and Technology of Lubricants,” 2nd Edition, London,Springer, Chapters 1 and 2 (1996); and A. Sequeria, Jr., “Lubricant BaseOil and Wax Processing,” New York, Marcel Decker, Chapter 6, (1994); andD. V. Brock, Lubrication Engineering, Vol. 43, pages 184-5, (1987), allof which are incorporated herein by reference. In certain embodiments,the amount of the base oil in the composition is greater than about 1%based on the total weight of the composition. In certain embodiments,the amount of the base oil in the composition is greater that about 2,5, 15 or 20% based on the total weight of the composition. In someembodiments, the amount of the base oil in the composition is from about1-20% based on the total weight of the composition. In certainembodiments, the amount of base oil in compositions provided herein isabout 1%, 5%, 7%, 10%, 13%, 15%, or 20% based on total weight of thecomposition.

In certain embodiments, the base oil is or comprises any natural orsynthetic lubricating base oil fraction. Some non-limiting examples ofsynthetic oils include oils, such as polyalphaolefins or PAOs, preparedfrom the polymerization of at least one alpha-olefin, such as ethylene,or from hydrocarbon synthesis procedures using carbon monoxide andhydrogen gases, such as the Fisher-Tropsch process.

In other embodiments, the base oil is or comprises a base stock or blendof base stocks. In further embodiments, the base stocks are manufacturedusing a variety of different processes including, but not limited to,distillation, solvent refining, hydrogen processing, oligomerization,esterification, and rerefining. In some embodiments, the base stockscomprise a rerefined stock. In further embodiments, the rerefined stockis substantially free from materials introduced through manufacturing,contamination, or previous use.

In some embodiments, the base oil comprises one or more of the basestocks in one or more of Groups I-V as specified in the AmericanPetroleum Institute (API) Publication 1509, Fourteen Edition, December1996 (i.e., API Base Oil Interchangeability Guidelines for Passenger CarMotor Oils and Diesel Engine Oils), which is incorporated herein byreference. The API guideline defines a base stock as a lubricantcomponent that may be manufactured using a variety of differentprocesses. Groups I, II and III base stocks are mineral oils, each withspecific ranges of the amount of saturates, sulfur content and viscosityindex. Group IV base stocks are polyalphaolefins (PAO). Group V basestocks include all other base stocks not included in Group I, II, III,or IV.

The saturates levels, sulfur levels and viscosity indices for Group I,II, III, IV and V base stocks are listed in Table 1 below.

TABLE 1 Viscosity Index (As Saturates (As Sulfur (As determined by ASTMD determined by determined by 4294, ASTM D 4297 or Group ASTM D 2007)ASTM D 2270) ASTM D 3120) I Less than 90% Greater than or Greater thanor equal to saturates. equal to 0.03% 80 and less than 120. sulfur. IIGreater than or Less than or Greater than or equal to equal to 90% equalto 0.03% 80 and less than 120. saturates. sulfur. III Greater than orLess than or Greater than or equal to equal to 90% equal to 0.03% 120.saturates. sulfur. IV Defined as polyalphaolefins (PAO) V All other basestocks not included in Groups I, II, III or IV

In certain embodiments, the base oil is selected from the groupconsisting of natural oils of lubricating viscosity, synthetic oils oflubricating viscosity and mixtures thereof. In some embodiments, thebase oil includes base stocks obtained by isomerization of synthetic waxand slack wax, as well as hydrocrackate base stocks produced byhydrocracking (rather than solvent extracting) the aromatic and polarcomponents of the crude. In other embodiments, the base oil oflubricating viscosity includes natural oils, such as animal oils,vegetable oils, mineral oils (e.g., liquid petroleum oils and solventtreated or acid-treated mineral oils of the paraffinic, naphthenic ormixed paraffinic-naphthenic types), oils derived from coal or shale, andcombinations thereof. Some non-limiting examples of animal oils includebone oil, lanolin, fish oil, lard oil, dolphin oil, seal oil, shark oil,tallow oil, and whale oil. Some non-limiting examples of vegetable oilsinclude castor oil, olive oil, peanut oil, rapeseed oil, corn oil,sesame oil, cottonseed oil, soybean oil, sunflower oil, safflower oil,hemp oil, linseed oil, tung oil, oiticica oil, jojoba oil, and meadowfoam oil. Such oils may be partially or fully hydrogenated.

In some embodiments, the synthetic oils of lubricating viscosity includehydrocarbon oils and halo-substituted hydrocarbon oils such aspolymerized and inter-polymerized olefins, alkylbenzenes, polyphenyls,alkylated diphenyl ethers, alkylated diphenyl sulfides, as well as theirderivatives, analogues and homologues thereof, and the like. In otherembodiments, the synthetic oils include alkylene oxide polymers,interpolymers, copolymers and derivatives thereof wherein the terminalhydroxyl groups can be modified by esterification, etherification, andthe like. In further embodiments, the synthetic oils include the estersof dicarboxylic acids with a variety of alcohols. In certainembodiments, the synthetic oils include esters made from C₅ to C₁₂monocarboxylic acids and polyols and polyol ethers. In furtherembodiments, the synthetic oils include tri-alkyl phosphate ester oils,such as tri-n-butyl phosphate and tri-iso-butyl phosphate.

In some embodiments, the synthetic oils of lubricating viscosity includesilicon-based oils (such as the polyakyl-, polyaryl-, polyalkoxy-,polyaryloxy-siloxane oils and silicate oils). In other embodiments, thesynthetic oils include liquid esters of phosphorus-containing acids,polymeric tetrahydrofurans, polyalphaolefins, and the like.

Base oil derived from the hydroisomerization of wax may also be used,either alone or in combination with the aforesaid natural and/orsynthetic base oil. Such wax isomerate oil is produced by thehydroisomerization of natural or synthetic waxes or mixtures thereofover a hydroisomerization catalyst.

In further embodiments, the base oil comprises a poly-alpha-olefin(PAO). In general, the poly-alpha-olefins may be derived from analpha-olefin having from about 2 to about 30, from about 4 to about 20,or from about 6 to about 16 carbon atoms. Non-limiting examples ofsuitable poly-alpha-olefins include those derived from octene, decene,mixtures thereof, and the like. These poly-alpha-olefins may have aviscosity from about 2 to about 15, from about 3 to about 12, or fromabout 4 to about 8 centistokes at 100° C. In some instances, thepoly-alpha-olefins may be used together with other base oils such asmineral oils.

In further embodiments, the base oil comprises a polyalkylene glycol ora polyalkylene glycol derivative, where the terminal hydroxyl groups ofthe polyalkylene glycol may be modified by esterification,etherification, acetylation and the like. Non-limiting examples ofsuitable polyalkylene glycols include polyethylene glycol, polypropyleneglycol, polyisopropylene glycol, and combinations thereof. Non-limitingexamples of suitable polyalkylene glycol derivatives include ethers ofpolyalkylene glycols (e.g., methyl ether of polyisopropylene glycol,diphenyl ether of polyethylene glycol, diethyl ether of polypropyleneglycol, etc.), mono- and polycarboxylic esters of polyalkylene glycols,and combinations thereof. In some instances, the polyalkylene glycol orpolyalkylene glycol derivative may be used together with other base oilssuch as poly-alpha-olefins and mineral oils.

In further embodiments, the base oil comprises any of the esters ofdicarboxylic acids (e.g., phthalic acid, succinic acid, alkyl succinicacids, alkenyl succinic acids, maleic acid, azelaic acid, suberic acid,sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonicacid, alkyl malonic acids, alkenyl malonic acids, and the like) with avariety of alcohols (e.g., butyl alcohol, hexyl alcohol, dodecylalcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycolmonoether, propylene glycol, and the like). Non-limiting examples ofthese esters include dibutyl adipate, di(2-ethylhexyl)sebacate,di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecylazelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, the2-ethylhexyl diester of linoleic acid dimer, and the like.

In further embodiments, the base oil comprises a hydrocarbon prepared bythe Fischer-Tropsch process. The Fischer-Tropsch process prepareshydrocarbons from gases containing hydrogen and carbon monoxide using aFischer-Tropsch catalyst. These hydrocarbons may require furtherprocessing in order to be useful as base oils. For example, thehydrocarbons may be dewaxed, hydroisomerized, and/or hydrocracked usingprocesses known to a person of ordinary skill in the art.

In further embodiments, the base oil comprises an unrefined oil, arefined oil, a rerefined oil, or a mixture thereof. Unrefined oils arethose obtained directly from a natural or synthetic source withoutfurther purification treatment. Non-limiting examples of unrefined oilsinclude shale oils obtained directly from retorting operations,petroleum oils obtained directly from primary distillation, and esteroils obtained directly from an esterification process and used withoutfurther treatment. Refined oils are similar to the unrefined oils exceptthe former have been further treated by one or more purificationprocesses to improve one or more properties. Many such purificationprocesses are known to those skilled in the art such as solventextraction, secondary distillation, acid or base extraction, filtration,percolation, and the like. Rerefined oils are obtained by applying torefined oils processes similar to those used to obtain refined oils.Such rerefined oils are also known as reclaimed or reprocessed oils andoften are additionally treated by processes directed to removal of spentadditives and oil breakdown products.

In certain embodiments, the compounds and compositions provided hereinhave use as pour point depressant additives. In another embodiment,provided herein are pour point depressant additive compositionscomprising a compound of formula I-A, I-B, I-C, I-D, II-A, II-B, II-C,II-D or a combination thereof and a compatible solvent. In oneembodiment, provided herein are pour point depressant additivecompositions comprising a farnesane dimer II-A or farnesane dimer II-B;a compound selected from squalane, squalene, and(6E,11E,18E)-2,6,19,23-tetramethyl-10,15-dimethylenetetracosa-2,6,11,18,22-pentaene;and a compatible solvent.

In certain embodiments, the compounds and compositions provided hereinare used in combination with one or more other additives known in theart, for example the following: detergents, particulate emissionreducers, storage stabilizers, antioxidants, corrosion inhibitors,dehazers, demulsifiers, antifoaming agents, cetane improvers,cosolvents, package compatibilizers, and lubricity additives.

In certain embodiments, the pour point depressant additive compositioncomprises between 0.1 and 75%, between 1 and 65%, or between 5 and 50%of the compound of formula I-A, I-B, I-C, I-D, II-A, II-B, II-C, II-D ora combination thereof in an oil or a solvent miscible with oil. Examplesof solvent are organic solvents including hydrocarbon solvents, forexample petroleum fractions such as naphtha, kerosene, diesel and heateroil; aromatic hydrocarbons; alcohols and/or esters; and paraffinichydrocarbons such as hexane and pentane and isoparaffins. The solvent isselected based on its compatibility with the additive and with the oil.Examples of oils for use herein include, crude oil or fuel oil. Incertain embodiments, the oil is a lubricating oil, which may be ananimal, vegetable or mineral oil, such as petroleum oil fractionsranging from naphthas or spindle oil to SAE 30, 40 or 50 lubricating oilgrades, castor oil, fish oils, oxidized mineral oil, or biodiesels. Thepour point depressant compositions provided herein are useful inlubricating oils as flow improvers, pour point depressants or dewaxingaids.

In certain embodiments, the compounds and compositions provided hereinhave use as fuel additives in fuels used to, for example, power internalcombustion engines such as reciprocating engines (e.g., gasoline enginesand diesel engines), Wankel engines, jet engines, some rocket engines,missile engines, and gas turbine engines. The compounds and compositionsprovided herein can be used in combination with other fuel additivesknown in the art. Types of fuel additives include, but are not limitedto, antioxidants, thermal stability improvers, cetane improvers,stabilizers, cold flow improvers, combustion improvers, anti-foams,anti-haze additives, corrosion inhibitors, lubricity improvers, icinginhibitors, injector cleanliness additives, smoke suppressants, dragreducing additives, metal deactivators, dispersants, detergents,demulsifiers, dyes, markers, static dissipaters, biocides, andcombinations thereof.

Methods of Preparation

The farnesene dimers and/or farnesane dimers for use in compositionsprovided herein can be prepared dimerization of β-farnesene as describedin Example 1. In some embodiments, β-farnesene is derived from anisoprenoid starting material. In certain embodiments, the isoprenoidstarting material is made by host cells by converting a carbon sourceinto the isoprenoid starting material. Exemplary methods for makingβ-farnesene are described in U.S. Pat. No. 7,399,323 B1 which isincorporated by reference in its entirety.

In certain embodiments, compounds I-A, I-B, I-C and I-D are prepared byinitiates a Diels Alder dimerization process by heating neat farneseneto temperatures above 120° C. Reaction of the vinyl group of the dienewith a second molecule of farnesene produces compounds I-A or I-Bdepending on the orientation of the dienophile. Reaction of theexo-methylene of farnesene with the diene of a second molecule resultsin the formation of compounds I-C or I-D, again depending on theorientation of the dienophile. In certain embodiments, compounds I-C andI-D come out just before compounds I-A and I-B with the ratio of peaksin order of elution being 1.00:1.46:5.67:5.02. This may vary a littlebit from run to run as measured by GC/MS. GC/FID integration is slightlydifferent in terms of ratios than the GC/MS. In certain embodiments, therelative ratios are the same but with slightly different magnitudes. Incertain embodiments, the ratios are: 1.00:1.24:4.51:3.93.

In certain embodiments, methods provided herein yield compositionscomprising farnesene dimers of formula I-A:I-B:I-C:I-D in a ratio of4:4:1:1. In certain embodiments, methods provided herein yieldcompositions comprising farnesane dimers of formula II-A:II-B:II-C:II-Din a ratio of 4:4:1:1.

In certain embodiments, the reaction yields are quantitative except forphysical losses if the crude product is filtered. In certainembodiments, the reaction is run from 150-240° C. In certainembodiments, the temperature for the reaction is between 180-200° C.

In certain embodiments, the hydrogenated dimers of formula II-A, II-B,II-C and II-D can be prepared by reducing the dimers of formula I-A,I-B, I-C and I-D in the presence of hydrogen with a catalyst such as Pd,Pd/C, Pt, PtO₂, Ru(PPh₃)₂Cl₂, Raney nickel, or combinations thereof. Inone embodiment, the catalyst is a Pd catalyst. In another embodiment,the catalyst is 5% Pd/C or 10% Pd/C. Alternatively, any reducing agentthat can reduce a C═C bond to a C—C bond can also be used. For example,hydrazine in the presence of a catalyst, such as5-ethyl-3-methyllumiflavinium perchlorate, under O₂ atmosphere can beused to give the corresponding hydrogenated products. The reductionreaction with hydrazine is disclosed in Imada et al., J. Am. Chem. Soc.,127, 14544-14545 (2005), which is incorporated herein by reference.

In certain embodiments, dehydrosqualene can be prepared from farneseneusing a suitable catalyst. Exemplary catalysts include Palladium (II)acetylacetonate and triphenylphosphine, combination of [Palladium (II)nitrate, sodium (2-methoxyphenoxide) or sodium phenoxide andtriphenylphosphine] (see e.g., BCS Japan, v. 51(4), p. 1156-62 (1978)and U.S. Pat. No. 3,859,374) as well as the combination of [bis(cyclooctadiene)nickel and tributylphosphine] (see U.S. Pat. No.3,794,692). In certain embodiments, polymer bound triphenylphosphine canbe used in place of soluble triphenylphosphine.

Squalane can be prepared by methods known in the art. In one embodiment,squalane can be prepared by reducing dehydrosqualene in the presence ofhydrogen with a catalyst such as Pd, Pd/C, Pt, PtO₂, Ru(PPh₃)₂Cl₂, Raneynickel, or combinations thereof.

The compositions disclosed herein can be prepared by any method known toa person of ordinary skill in the art for making lubricating oils. Insome embodiments, one or more farnesene dimers in the lubricating oilcompositions are blended or mixed with other components, such as one ormore lubricating oil additives.

In some embodiments, the farnesene dimers or farnesane dimers areblended or mixed with squalane, squalene or dehydrosqualene to obtain alubricating oil composition. In certain embodiments, the lubricating oilcompositions are further blended or mixed with other components, such asone or more lubricating oil additives.

Exemplary lubricating oil additives are described below. Any mixing ordispersing equipment known to a person of ordinary skill in the art maybe used for blending, mixing or solubilizing the ingredients.

The following additive components are examples of some of the componentsthat can be added to compositions provided herein. These examples ofadditives are provided to illustrate the compositions, but they are notintended to limit them.

Additives

Optionally, the composition may further comprise at least one additiveor a modifier (hereinafter designated as “additive”) that can impart orimprove any desirable property of the composition. In certainembodiments, the additive is a lubricating oil additive. Any lubricatingoil additive known to a person of ordinary skill in the art may be usedin the compositions disclosed herein. Some suitable additives have beendescribed in Mortier et al., “Chemistry and Technology of Lubricants,”2nd Edition, London, Springer, (1996); and Leslie R. Rudnick, “LubricantAdditives: Chemistry and Applications,” New York, Marcel Dekker (2003),both of which are incorporated herein by reference. In some embodiments,the additive can be selected from the group consisting of antioxidants,antiwear agents, detergents, rust inhibitors, demulsifiers, frictionmodifiers, multi-functional additives, pour point depressants, foaminhibitors, metal deactivators, dispersants, corrosion inhibitors,thermal stability improvers, dyes, markers, and combinations thereof.

In general, the concentration of each of the additives in thecomposition, when used, may range from about 0.001 wt. % to about 20 wt.%, from about 0.01 wt. % to about 10 wt. %, from about 0.1 wt. % toabout 5 wt. % or from about 0.1 wt. % to about 2.5 wt. %, based on thetotal weight of the composition. Further, the total amount of theadditives in the composition may range from about 0.001 wt. % to about30 wt. %, from about 0.01 wt. % to about 20 wt. %, from about 0.1 wt. %to about 10 wt. %, or from about 0.1 wt. % to about 5 wt. %, based onthe total weight of the composition.

Metal Detergents

In some embodiments, a composition provided herein comprises at least aneutral or overbased metal detergent as an additive, or additivecomponents. In certain embodiments, the metal detergent prevents theformation of deposits on the surface of an engine. In certainembodiments, the detergent have additional functions, for example, asantioxidant. In certain aspects, compositions contain metal detergentscomprising either overbased detergents or mixtures of neutral andoverbased detergents. The term “overbased” is intended to defineadditives which contain a metal content in excess of that required bythe stoichiometry of the particular metal and the particular organicacid used. The excess metal exists in the form of particles of inorganicbase, e.g. a hydroxide or carbonate, surrounded by a sheath of metalsalt. The sheath serves to maintain the particles in dispersion in aliquid oleaginous vehicle. The amount of excess metal is commonlyexpressed as the ratio of total equivalence of excess metal toequivalence of organic acid and is typically 0.1 to 30.

Some non-limiting examples of suitable metal detergents includesulfurized or unsulfurized alkyl or alkenyl phenates, alkyl or alkenylaromatic sulfonates, borated sulfonates, sulfurized or unsulfurizedmetal salts of multi-hydroxy alkyl or alkenyl aromatic compounds, alkylor alkenyl hydroxy aromatic sulfonates, sulfurized or unsulfurized alkylor alkenyl naphthenates, metal salts of alkanoic acids, metal salts ofan alkyl or alkenyl multiacid, and chemical and physical mixturesthereof. Other non-limiting examples of suitable metal detergentsinclude metal sulfonates, phenates, salicylates, phosphonates,thiophosphonates and combinations thereof. The metal can be any metalsuitable for making sulfonate, phenate, salicylate or phosphonatedetergents. Non-limiting examples of suitable metals include alkalimetals, alkaline metals and transition metals. In some embodiments, themetal is Ca, Mg, Ba, K, Na, Li or the like. An exemplary metal detergentwhich may be employed in the compositions includes overbased calciumphenate.

Generally, the amount of the metal detergent additive can be less than10000 ppm, less than 1000 ppm, less than 100 ppm, or less than 10 ppm,based on the total weight of the composition. In some embodiments, theamount of the metal detergent is from about 0.001 wt. % to about 5 wt.%, from about 0.05 wt. % to about 3 wt. %, or from about 0.1 wt. % toabout 1 wt. %, based on the total weight of the composition. Somesuitable detergents have been described in Mortier et al., “Chemistryand Technology of Lubricants,” 2nd Edition, London, Springer, Chapter 3,pages 75-85 (1996); and Leslie R. Rudnick, “Lubricant Additives:Chemistry and Applications,” New York, Marcel Dekker, Chapter 4, pages113-136 (2003), both of which are incorporated herein by reference.

Solubilizing Agents

Solubilizing agents may be used in compositions provided herein toincrease solubility of various components in the composition. Suitablesolubilizing agents include, but are not limited to, oil-soluble estersand diesters, alkylated naphthalenes, alkylated sulfones, naphthenictype base oils, aromatic type base oils, and alkylated benzenes. Othersolubilizing agents known in the art are also contemplated herein. Theesters and diesters that may be used as solublizing agents include, forexample, adipate esters and polyol esters. Exemplary diesters includethe adipates, azelates, and sebacates of C₈-C₁₃ alkanols (or mixturesthereof), the phthalates of C₄-C₁₃ alkanols (or mixtures thereof).Mixtures of two or more different types of diesters (e.g., dialkyladipates and dialkyl azelates, etc.) may also be used. Examples of suchmaterials include the n-octyl, 2-ethylhexyl, isodecyl, and tridecyldiesters of adipic acid, azelaic acid, and sebacic acid, and then-butyl, isobutyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl,dodecyl, and tridecyl diesters of phthalic acid.

Anti Wear and/or Extreme Pressure Agents

In certain embodiments, compositions disclosed herein can additionallycomprise anti wear or extreme pressure agents. Wear occurs in allequipment that has moving parts in contact. Specifically, threeconditions commonly lead to wear in engines: (1) surface-to-surfacecontact; (2) surface contact with foreign matter; and (3) erosion due tocorrosive materials. Wear resulting from surface-to-surface contact isfriction or adhesive wear, from contact with foreign matter is abrasivewear, and from contact with corrosive materials is corrosive wear.Fatigue wear is an additional type of wear that is common in equipmentwhere surfaces are not only in contact but also experience repeatedstresses for prolonged periods. Abrasive wear can be prevented byinstalling an efficient filtration mechanism to remove the offendingdebris. Corrosive wear can be addressed by using additives whichneutralize the reactive species that would otherwise attack the metalsurfaces. The control of adhesive wear requires the use of additivescalled antiwear and extreme-pressure (EP) agents.

Under optimal conditions of speed and load, the metal surfaces of theequipment should be effectively separated by a lubricant film.Increasing load, decreasing speed, or otherwise deviating from suchoptimal conditions promote metal-to-metal contact. This contacttypically causes a temperature increase in the contact zone due tofrictional heat, which in turn leads to the loss of lubricant viscosityand hence its film-forming ability. In certain embodiments, antiwearadditive and EP agents offer protection by a similar mechanism. Incertain embodiments, EP additives require higher activation temperaturesand load than antiwear additives.

Without being bound to any particular theory, it is believed thatantiwear and/or EP additives function by thermal decomposition and byforming products that react with the metal surface to form a solidprotective layer. This solid metal film fills the surface asperities andfacilitates effective film formation, thereby reducing friction andpreventing welding and surface wear.

Most antiwear and extreme pressure agents contain sulfur, chlorine,phosphorus, boron, or combinations thereof. The classes of compoundsthat inhibit adhesive wear include, for example, alkyl and aryldisulfides and polysulfides; dithiocarbamates; chlorinated hydrocarbons;and phosphorus compounds such as alkyl phosphites, phosphates,dithiophosphates, and alkenylphosphonates.

Exemplary antiwear agents that can be included in compositions providedherein include metal (e.g., Pb, Sb, and the like) salts ofdithiophosphate, metal (e.g., Pb, Sb, and the like) salts ofdithiocarbamate, metal (e.g., Pb, Sb and the like) salts of fatty acids,boron compounds, phosphate esters, phosphite esters, amine salts ofphosphoric acid esters or thiophosphoric acid esters, reaction productsof dicyclopentadiene and thiophosphoric acids and combinations thereof.The amount of the anti-wear agent may vary from about 0.01 wt. % toabout 5 wt. %, from about 0.05 wt. % to about 3 wt. %, or from about 0.1wt. % to about 1 wt. %, based on the total weight of the composition.Some suitable anti-wear agents have been described in Leslie R. Rudnick,“Lubricant Additives: Chemistry and Applications,” New York, MarcelDekker, Chapter 8, pages 223-258 (2003), which is incorporated herein byreference.

In one embodiment, the sulfated ash content of the total composition isless than 5 wt. %, less than 4 wt. %, less than 3 wt. %, less than 2 wt.%, or less than 1 wt. %, as measured according to ASTM D874.

In one embodiment, the EP agents for use in compositions provided hereininclude alkyl and aryl disulfides and polysulfides, dithiocarbamates,chlorinated hydrocarbons, dialkyl hydrogen phosphites, and salts ofalkyl phosphoric acids. Methods of making these EP agents are known inthe art. For example, polysulfides are synthesized from olefins eitherby reacting with sulfur or sulfur halides, followed bydehydrohalogenation. Dialkydithiocarbamates are prepared either byneutralizing dithiocarbamic acid (which can be prepared by reacting adiakylamine and carbon disulfide at low temperature) with bases, such asantimony oxide, or by its addition to activated olefins, such as alkylacrylates.

In certain embodiments, compositions provided herein comprise one ormore EP agents. In one embodiment, use of more that one EP agent leadsto synergism. For example, synergism may be observed between sulfur andchlorine-containing EP agents. An exemplary composition provided hereinincludes one or more EP agents selected from: zincdialkyldithiophosphate (primary alkyl type & secondary alkyl type),sulfurized oils, diphenyl sulfide, methyl trichlorostearate, chlorinatednaphthalene, fluoroalkylpolysiloxane, and lead naphthenate.

Rust Inhibitors (Anti Rust Agents)

Protection against rust is an important consideration in formulatinglubricants. Without protection, rust ultimately causes a loss of metal,thereby lowering the integrity of the equipment, and resulting in enginemalfunction. In addition, corrosion exposes fresh metal that can wear atan accelerated rate, perpetuated by the metal ions that might bereleased into the fluid and act as oxidation promoters.

The composition disclosed herein can optionally comprise a rustinhibitor that can inhibit the corrosion of metal surfaces. Any rustinhibitor known by a person of ordinary skill in the art may be used inthe composition. The rust inhibitors attach themselves to metal surfacesto form an impenetrable protective film, which can be physically orchemically adsorbed to the surface. Specifically, film formation occurswhen the additives interact with the metal surface via their polar endsand associate with the lubricant via their nonpolar ends. Suitable rustinhibitors may include, for example, various nonionic polyoxyethylenesurface active agents such as polyoxyethylene lauryl ether,polyoxyethylene higher alcohol ether, polyoxyethylene nonylphenyl ether,polyoxyethylene octylphenyl ether, polyoxyethylene octyl stearyl ether,polyoxyethylene oleyl ether, polyoxyethylene sorbitol monostearate,polyoxyethylene sorbitol mono-oleate, and polyethylene glycolmonooleate. Suitable rust inhibitors may further include other compoundssuch as, for example, monocarboxylic acids (e.g., 2-ethylhexanoic acid,lauric acid, myristic acid, palmitic acid, oleic acid, linoleic acid,linolenic acid, behenic acid, cerotic acid and the like), oil-solublepolycarboxylic acids (e.g., those produced from tall oil fatty acids,oleic acid, linoleic acid and the like), alkenylsuccinic acids in whichthe alkenyl group contains 10 or more carbon atoms (e.g.,tetrapropenylsuccinic acid, tetradecenylsuccinic acid,hexadecenylsuccinic acid, and the like); long-chain alpha,omega-dicarboxylic acids having a molecular weight in the range of 600to 3000 daltons and combinations thereof. Further examples of rustagents include metal soaps, fatty acid amine salts, metal salts of heavysulfonic acid, partial carboxylic acid ester of polyhydric alcohol, andphosphoric ester.

Demulsifiers

The composition disclosed herein can optionally comprise a demulsifierthat can promote oil-water separation in compositions that are exposedto water or steam. Any demulsifier known by a person of ordinary skillin the art may be used in the composition. Non-limiting examples ofsuitable demulsifiers include anionic surfactants (e.g.,alkyl-naphthalene sulfonates, alkyl benzene sulfonates and the like),nonionic alkoxylated alkylphenol resins, polymers of alkylene oxides(e.g., polyethylene oxide, polypropylene oxide, block copolymers ofethylene oxide, propylene oxide and the like), esters of oil solubleacids, polyoxyethylene sorbitan ester and combinations thereof. Incertain embodiments, the demulsifiers for use herein include blockcopolymers of propylene oxide or ethylene oxide and initiators, such as,for example, glycerol, phenol, formaldehyde resins, soloxanes,polyamines, and polyols. In certain embodiments, the polymers containabout 20 to about 50% ethylene oxide. These materials concentrate at thewater-oil interface and create low viscosity zones, thereby promotingdroplet coalescence and gravity-driven phase separation. Low molecularweight materials, such as, for example, alkali metal or alkaline earthmetal salts of dialkylnaphthalene sulfonic acids, are also useful incertain applications. The amount of the demulsifier may vary from about0.01 wt. % to about 10 wt. %, from about 0.05 wt. % to about 5 wt. %, orfrom about 0.1 wt. % to about 3 wt. %, based on the total weight of thecomposition. Some suitable demulsifiers have been described in Mortieret al., “Chemistry and Technology of Lubricants,” 2nd Edition, London,Springer, Chapter 6, pages 190-193 (1996), which is incorporated hereinby reference.

Friction Modifiers

The composition disclosed herein can optionally comprise a frictionmodifier that can lower the friction between moving parts. Any frictionmodifier known by a person of ordinary skill in the art may be used inthe composition. They are typically long-chain molecules with a polarend group and a nonpolar linear hydrocarbon chain. The polar end groupseither physically adsorb onto the metal surface or chemically react withit, while the hydrocarbon chain extends into the lubricant. The chainsassociated with one another and the lubricant to form a strong lubricantfilm.

Non-limiting examples of suitable friction modifiers include fattycarboxylic acids; derivatives (e.g., alcohol, esters, borated esters,amides, metal salts and the like) of fatty carboxylic acid; mono-, di-or tri-alkyl substituted phosphoric acids or phosphonic acids;derivatives (e.g., esters, amides, metal salts and the like) of mono-,di- or tri-alkyl substituted phosphoric acids or phosphonic acids;mono-, di- or tri-alkyl substituted amines; mono- or di-alkylsubstituted amides and combinations thereof.

In one embodiment, the friction modifier is a saturated fatty acidcontaining a 13 to 18 carbon chains. The amount of the friction modifiermay vary from about 0.01 wt. % to about 10 wt. %, from about 0.05 wt. %to about 5 wt. %, or from about 0.1 wt. % to about 3 wt. %, based on thetotal weight of the composition. Some suitable friction modifiers havebeen described in Mortier et al., “Chemistry and Technology ofLubricants,” 2nd Edition, London, Springer, Chapter 6, pages 183-187(1996); and Leslie R. Rudnick, “Lubricant Additives: Chemistry andApplications,” New York, Marcel Dekker, Chapters 6 and 7, pages 171-222(2003), both of which are incorporated herein by reference.

Seal Swell Agents

Seal swell agents may be included in the finished compositions of thedisclosed embodiments particularly when compositions provided herein areused as power transmission fluids. Suitable seal swell agents may beselected from oil-soluble diesters, oil-soluble sulfones, siliconcontaining organic compounds, and mixtures thereof. Generally speakingthe most suitable diesters include the adipates, azelates, and sebacatesof C₈-C₁₃ alkanols (or mixtures thereof), and the phthalates of C₄-C₁₃alkanols (or mixtures thereof). Mixtures of two or more different typesof diesters (e.g., dialkyl adipates and dialkyl azelates, etc.) may alsobe used. Examples of such materials include the n-octyl, 2-ethylhexyl,isodecyl, and tridecyl diesters of adipic acid, azelaic acid, andsebacic acid, and the n-butyl, isobutyl, pentyl, hexyl, heptyl, octyl,nonyl, decyl, undecyl, dodecyl, and tridecyl diesters of phthalic acid.Other esters which may give generally equivalent performance are polyolesters.

In one embodiment, the seal swell agents are the oil-soluble dialkylesters of (i) adipic acid, (ii) sebacic acid, or (iii) phthalic acid.

Pour Point Depressants

The composition disclosed herein can optionally comprise a pour pointdepressant that can lower the pour point of the composition. Any pourpoint depressant known by a person of ordinary skill in the art may beused in the composition. In certain embodiments, pour point depressantspossess one or more structural features selected from: (1) polymericstructure; (2) waxy and non-waxy components; (3) comb structurecomprising a short backbone with long pendant groups; and (4) broadmolecular weight distribution. Non-limiting examples of suitable pourpoint depressants include polymethacrylates, alkyl acrylate polymers,alkyl methacrylate polymers, alkyl fumarate polymers, di(tetra-paraffinphenol)phthalate, condensates of tetra-paraffin phenol, condensates of achlorinated paraffin with naphthalene, alkylated naphthalenes, styreneesters, oligomerized alkyl phenols, phthalic acid esters, ethylene-vinylacetate copolymers and combinations thereof. In one embodiment, the pourpoint depressant is selected from tetra (long-chain) alkyl silicates,phenyltristearyloxysilane, and pentaerythritol tetrastearate. In someembodiments, the pour point depressant comprises an ethylene-vinylacetate copolymer, a condensate of chlorinated paraffin and phenol,polyalkyl styrene or the like. The amount of the pour point depressantmay vary from about 0.01 wt. % to about 10 wt. %, from about 0.05 wt. %to about 5 wt. %, or from about 0.1 wt. % to about 3 wt. %, based on thetotal weight of the composition. Some suitable pour point depressantshave been described in Mortier et al., “Chemistry and Technology ofLubricants,” 2nd Edition, London, Springer, Chapter 6, pages 187-189(1996); and Leslie R. Rudnick, “Lubricant Additives: Chemistry andApplications,” New York, Marcel Dekker, Chapter 11, pages 329-354(2003), both of which are incorporated herein by reference.

Foam Inhibitors

The composition disclosed herein can optionally comprise a foaminhibitor or an anti-foam that can break up foams in oils. Any foaminhibitor or anti-foam known by a person of ordinary skill in the artmay be used in the composition. Non-limiting examples of suitableanti-foams include silicone oils or polydimethylsiloxanes,fluorosilicones, alkoxylated aliphatic acids, polyethers (e.g.,polyethylene glycols), branched polyvinyl ethers, alkyl acrylatepolymers, alkyl methacrylate polymers, polyalkoxyamines and combinationsthereof. In some embodiments, the anti-foam comprises glycerolmonostearate, polyglycol palmitate, a trialkyl monothiophosphate, anester of sulfonated ricinoleic acid, benzoylacetone, methyl salicylate,glycerol monooleate, or glycerol dioleate. The amount of the anti-foammay vary from about 0.01 wt. % to about 5 wt. %, from about 0.05 wt. %to about 3 wt. %, or from about 0.1 wt. % to about 1 wt. %, based on thetotal weight of the composition. Some suitable anti-foams have beendescribed in Mortier et al., “Chemistry and Technology of Lubricants,”2nd Edition, London, Springer, Chapter 6, pages 190-193 (1996), which isincorporated herein by reference.

Metal Deactivators

In some embodiments, the composition comprises at least a metaldeactivator. Some non-limiting examples of suitable metal deactivatorsinclude disalicylidene propylenediamine, triazole derivatives,thiadiazole derivatives, and mercaptobenzimidazoles.

Dispersants

The composition disclosed herein can optionally comprise a dispersantthat can prevent sludge, varnish, and other deposits by keepingparticles suspended in a colloidal state. In certain embodiments,dispersants perform these functions via one or more means selected from:(1) solubilizing polar contaminants in their micelles; (2) stabilizingcolloidal dispersions in order to prevent aggregation of their particlesand their separation out of oil; (3) suspending such products, if theyform, in the bulk lubricant; (4) modifying soot to minimize itsaggregation and oil thickening; and (5) lowering surface/interfacialenergy of undesirable materials to decrease their tendency to adhere tosurfaces. The undesirable materials are typically formed as a result ofoxidative degradation of the lubricant, the reaction of chemicallyreactive species such as carboxylic acids with the metal surfaces in theengine, or the decomposition of thermally unstable lubricant additivessuch as, for example, extreme pressure agents.

In certain aspects, a dispersant molecule comprises three distinctstructural features: (1) a hydrocarbyl group; (2) a polar group; and (3)a connecting group or a link. In certain embodiments, the hydrocarbylgroup is polymeric in nature, and has a molecular weight of at or aboveabout 2000 Daltons, in one embodiment, at or above about 3000 Daltons,in another embodiment, at or above about 5000 Daltons, and in yetanother embodiment, at or above about 8000 Daltons. A variety ofolefins, such as polyisobutylene, polypropylene, polyalphaolefins, andmixtures thereof, can be used to make suitable polymeric dispersants. Incertain embodiments, the polymeric dispersant is apolyisobutylene-derived dispersant. Typically the number averagemolecular weight of polyisobutylene in those dispersants ranges betweenabout 500 and about 3000 Daltons, or, in some embodiments, between about800 to about 2000 Daltons, or in further embodiments, between about 1000to about 2000 Daltons. In certain embodiments, the polar group in thedispersant is nitrogen- or oxygen-derived. Nitrogen-based dispersantsare typically derived from amines. The amines from which thenitrogen-based dispersants are derived are often polyalkylenepolyamines,such as, for example, diethylenetriamine and trethylenetetramine.Amine-derived dispersants are also called nitrogen- oramine-dispersants, while those derived from alcohol are also calledoxygen or ester dispersants. Oxygen-based dispersants are typicallyneutral while the amine-based dispersants are typically basic.

Non-limiting examples of suitable dispersants include alkenylsuccinimides, alkenyl succinimides modified with other organiccompounds, alkenyl succinimides modified by post-treatment with ethylenecarbonate or boric acid, succinamides, succinate esters, succinateester-amides, pentaerythritols, phenate-salicylates and theirpost-treated analogs, alkali metal or mixed alkali metal, alkaline earthmetal borates, dispersions of hydrated alkali metal borates, dispersionsof alkaline-earth metal borates, polyamide ashless dispersants,benzylamines, Mannich type dispersants, phosphorus-containingdispersants, and combinations thereof. The amount of the dispersant mayvary from about 0.01 wt. % to about 10 wt. %, from about 0.05 wt. % toabout 7 wt. %, or from about 0.1 wt. % to about 4 wt. %, based on thetotal weight of the composition. Some suitable dispersants have beendescribed in Mortier et al., “Chemistry and Technology of Lubricants,”2nd Edition, London, Springer, Chapter 3, pages 86-90 (1996); and LeslieR. Rudnick, “Lubricant Additives: Chemistry and Applications,” New York,Marcel Dekker, Chapter 5, pages 137-170 (2003), both of which areincorporated herein by reference.

Anti-Oxidants

Optionally, the composition disclosed herein can further comprise anadditional antioxidant that can reduce or prevent the oxidation of thebase oil. Any antioxidant known by a person of ordinary skill in the artmay be used in the composition. Examples of anti oxidants useful incompositions provided herein include, but are not limited to, phenoltype (phenolic) oxidation inhibitors, such as 4,4′ methylene bis(2,6 ditert butylphenol), 4,4′ bis(2,6 di tert-butylphenol), 4,4′ bis (2 methyl6 tert butylphenol), 2,2′ methylene bis(4-methyl 6 tert butylphenol),4,4′ butylidene bis (3 methyl 6 tert butylphenol), 4,4′ isopropylidenebis(2,6 di tert butylphenol), 2,2′ methylene bis(4-methyl 6nonylphenol), 2,2′ isobutylidene bis(4,6 dimethylphenol), 2,2′ 5methylene bis (4 methyl 6 cyclohexylphenol), 2,6 di tert butyl4-methylphenol, 2,6 di tert butyl 4 ethylphenol, 2,4 dimethyl 6 tertbutyl-phenol, 2,6 di tert 1 dimethylamino p cresol, 2,6 di tert 4(N,N′-dimethylaminomethylphenol), 4,4′ thiobis (2 methyl 6 tertbutylphenol), 2,2′-thiobis (4 methyl 6 tert butylphenol), bis (3 methyl4 hydroxy 5 tert-10 butylbenzyl)sulfide, and bis(3,5 di tert butyl 4hydroxybenzyl). Diphenylamine type oxidation inhibitors include, but arenot limited to, alkylated diphenylamine, phenyl alpha naphthylamine, andalkylated alpha naphthylamine, sulfur-based antioxidants (e.g.,dilauryl-3,3′-thiodipropionate, sulfurized phenolic antioxidants and thelike), phosphorous-based antioxidants (e.g., phosphites and the like),zinc dithiophosphate, oil-soluble copper compounds and combinationsthereof. Other types of oxidation inhibitors include metaldithiocarbamate (e.g., zinc dithiocarbamate), and 15methylenebis(dibutyldithiocarbamate). The amount of the antioxidant mayvary from about 0.01 wt. % to about 10 wt. %, from about 0.05 wt. % toabout 5 wt. %, or from about 0.1 wt. % to about 3 wt. %, based on thetotal weight of the composition. Some suitable antioxidants have beendescribed in Leslie R. Rudnick, “Lubricant Additives: Chemistry andApplications,” New York, Marcel Dekker, Chapter 1, pages 1-28 (2003),which is incorporated herein by reference.

Multifunctional Additives

Various additives mentioned or not mentioned herein can provide amultiplicity of effects to the lubricant oil composition providedherein. Thus, for example, a single additive may act as a dispersant aswell as an oxidative inhibitor. Multi-functional additives are wellknown in the art. Other suitable multi-functional additives may include,for example, sulfurized oxymolybdenum dithiocarbamate, sulfurizedoxymolybdenum organo pohosphoro dithioate, oxymolybdenum monoglyceride,amine-molybdenum complex compound, and sulfur-containing molybdenumcomplex compounds.

Viscosity Index Improvers

In certain embodiments, the composition comprises at least a viscosityindex improver. Some non-limiting examples of suitable viscosity indeximprovers include polymethacrylate type polymers, ethylene-propylenecopolymers, styrene-isoprene copolymers, hydrated styrene-isoprenecopolymers, polyisobutylene, and dispersant type viscosity indeximprovers.

Conductivity Enhancers

In certain embodiments, the composition comprises at least aconductivity enhancer. Some non-limiting examples of suitableconductivity enhancers include hydrogenated lecithin and relatedcompounds; magnesium palmitate or aluminum palmitate or stearate;dihexyl esters of phosphoric acid neutralized withtetramethylnonylamines or C11 -C14-alkylamines; monosodium phosphatederivatives of mono- and diglycerides composed of glyceride derivativesformed by reacting mono- and diglycerides that are derived from ediblesources with phosphorus pentoxide (tetraphosphorus decoxide) followed byneutralization with sodium carbonate; phosphate derivatives of mono- anddiglycerides produced as described above and reacted with ethanolamineand neutralized with fatty acid, and sodium dodecyl sulfonate.

Load-Bearing Additives

In certain embodiments, the composition comprises one or moreload-bearing additives to reduce friction during metal work processing.Exemplary load-bearing additives include, but are not limited to fattyalcohols, dicarboxylic acids or fatty acids and esters thereof, forinstance fatty acid esters, butyl stearate, butyl palmitate, tridecylazelate and/or dioctyl sebacate.

Uses of the Compositions

The compositions provided herein are used in a wide variety ofindustrial applications associated with the automotive, tractor,airline, and railroad industries for use in engine oils, transmissionfluids, hydraulic fluids, gear oils, energy/shock absorbers powersteering; metal-working industry for use in metal sheets rolling orcutting machines and water coolants; process oils for use in rubber andplastic processing; marine oils for use in propel engines; quenchfluids; greases; crankcase lubricants; vehicle axle applications; androtating machinery such as stationary engines, pumps, gas turbines,compressors, wind turbines, and the like. Stationary engines includefuel and gas powered engines that are not associated with theautomotive, tractor, airline, and railroad industries. Exemplaryautomotive applications include, but are not limited to use in engineoils, for example, internal combustion engines, natural gas engines,turbine engines, automatic and manual transmissions and marine dieselengines. In certain embodiments, compositions provided herein have useas industrial oils, such as in hydraulic oils, fire-resistant oils,industrial gear oils, railroad diesel and natural gas. In addition, theproducts based on embodiments described herein may be used in planetaryhub reduction axles, mechanical steering and transfer gear boxes inutility vehicles such as trucks, synchromesh gear boxes, as well aspower take-off gears, limited slip axles, and planetary hub reductiongear boxes.

In one embodiment, compositions provided herein are useful as enginelubricants. In one embodiment, provided herein is a method oflubricating an engine comprising operating the engine in contact with acomposition provided herein.

In certain embodiments, provided herein is a method of lubricating amachine by operating the machine in contact with a composition providedherein. The compositions can be used for lubricating any machine thatneeds lubrication. Exemplary machines include, but are not limited toengines, pumps, gas turbines, compressors, wind turbines, and the like.In certain embodiments, the engine is a fuel and/or gas powered engineassociated with the automotive, tractor, airline, and railroadindustries. In certain embodiments, the engine is a stationary engine,including a fuel and/or gas powered engine that is not associated withthe automotive, tractor, airline, and railroad industries. In certainembodiments, provided herein is a machine comprising a compositionprovided herein.

In one embodiment, a composition provided herein is an automatictransmission fluid (ATF). An exemplary ATF composition contains one ormore farnesene dimers and/or farnesane dimers provided herein, asolubilizing agent, from about 0.5 to about 1.5 wt. % viscosity indeximprover, from about 1.5 to about 2.5 wt. % ashless dispersant, fromabout 0.05 to about 1 wt. % friction modifier, from about 0.01 to about0.5 wt. % corrosion inhibitor, from about 0.1 to about 0.4 wt. %antiwear additive, from about 0.005 to about 5 wt. % metal deactivator,from about 0.1 to about 15 wt. % metallic detergent, from about 0.25 toabout 1 wt. % seal swell agent, from about 0.01 to about 0.5 wt. % pourpoint depressant and optionally a base oil component.

In one embodiment, the finished composition is a manual transmissionoil. An exemplary manual transmission lubricating oil formulationcontains one or more farnesene dimers and/or farnesane dimers providedherein, a solubilizing agent, a viscosity index improver, an ashlessdispersant, at least one antioxidant, at least one inhibitor andoptionally a base oil component.

In another embodiment of the disclosure, the finished composition is anaxle lubricating oil. An exemplary axle lubricating oil formulationcontains a solubilizing agent, a viscosity index improver, a sulfurcontaining extreme pressure agent, at least one phosphorus containinganti-wear agent, at least one ashless dispersant, at least one inhibitorand optionally a base oil component.

In one embodiment, compositions provided herein are used as a crankcaselubricant and may include a solubilizing agent, a viscosity indeximprover, a detergent, a dispersant, an anti-wear agent, a frictionmodifier, an antioxidant, a corrosion inhibitor, a pour pointdepressant, an anti-foam agent and optionally a base oil component.

The compositions described herein may also be used in quench fluidapplications to provide a slower rate of cooling for hardening metalssuch as steel. Quench fluid performance may be modified by introducingone or more of the foregoing additives and/or compositions to improvewettability, cooling rates, oil stability life, and to reduce depositforming tendencies of the quench fluids.

While the compounds, compositions and methods have been described withrespect to a limited number of embodiments, the specific features of oneembodiment should not be attributed to other embodiments describedherein. No single embodiment is representative of all aspects of thecompositions or methods. In some embodiments, the compositions ormethods may include numerous compounds or steps not mentioned herein. Inother embodiments, the compositions or methods do not include, or aresubstantially free of, any compounds or steps not enumerated herein.Variations and modifications from the described embodiments exist.

All publications and patent applications mentioned in this specificationare herein incorporated by reference to the same extent as if eachindividual publication or patent application was specifically andindividually indicated to be incorporated by reference. Although theforegoing has been described in some detail by way of illustration andexample for purposes of clarity of understanding, it will be readilyapparent to those of ordinary skill in the art in light of the teachingsherein that certain changes and modifications may be made theretowithout departing from the spirit or scope of the appended claims.

EXAMPLES

The practice of the present subject matter can employ, unless otherwiseindicated, conventional techniques in the industry and the like, whichare within the skill of the art. To the extent such techniques are notdescribed fully herein, one can find ample reference to them in thescientific literature.

In the following examples, efforts have been made to ensure accuracywith respect to numbers used (for example, amounts, temperature, and soon), but variation and deviation can be accommodated, and in the event aclerical error in the numbers reported herein exists, one of ordinaryskill in the arts can deduce the correct amount in view of the remainingdisclosure herein. Unless indicated otherwise, temperature is reportedin degrees Celsius. All reagents, unless otherwise indicated, wereobtained commercially. β-farnesene used herein is prepared as describedin U.S. Pat. No. 7,399,323 B1 which is incorporated by reference in itsentirety. The following examples are intended for illustrative purposesonly and do not limit in any way the scope of the present invention.

Example 1

This example describes a method for making farnesene dimers fromβ-farnesene.

To a 500 mL three-necked round-bottomed flask, previously rinsed withconc. NH₄OH solution and dried, equipped with a magnetic stirrer,heating mantle, thermometer, reflux condenser and nitrogen inlet wereadded 204 g (1.00 mol) of β-farnesene (Bedoukian, 98%). The farnesenewas stirred and heated to 220° C. while monitoring the progress of thereaction by GC/MS. After two hours the colorless reaction mixtureconsisted almost entirely of two pairs of dimers, I-A:I-C in a ratio of4:1 and I-B:I-D in a ratio of 4:1 with <2% of starting materialremaining. The mixture was allowed to cool to approximately 50° C. andvacuum filtered through a 0.5 cm thick layer of Celite on a 60 mL mediumporosity sintered glass funnel to afford 200 g (98:3%) of clearcolorless oil. The compositions comprise compounds I-A, I-C, I-B, andI-D which was confirmed by ¹H and ¹³C NMR.

Farnesene dimers: ¹H (400 MHz, CDCl₃) d (multiplicity, couplingconstant{s}, integration*), 5.71 (dd, J=5.6 and 10.8 Hz, 0.04H), 5.65(dd, J=5.6 and 10.8 Hz, 0.04H), 5.37 (m, 0.60H), 5.12 (m, 3.04H), 5.01(dt, J=1.6 and 10.8 Hz, 0.10H), 4.89 (ddd, J=1.6, 12.0 and 17.6 Hz,0.06H), 4.74 (m, 1.00H), 2.09 (m, 9.28H), 1.98 (m, 5.30H), 1.68 (s,4.24H), 1.60 (s, 7.97H) ppm. * Integration values are relative areaspeak to peak and not absolute numbers of protons.

Farnesene dimers: ¹³C (100 MHz, CDCl₃) d 154.36, 154.26, 146.14, 145.44,145.25, 139.55, 139.04, 137.46, 137.39, 136.94, 135.87, 135.38, 135.11,135.07, 134.94, 134.82, 134.59, 131.225, 125.01, 124.97, 124.44, 124.34,124.23, 124.06, 122.71, 120.47, 120.37, 120.17, 119.16, 115.71, 113.02,112.11, 112.01, 107.24, 107.18, 40.39, 40.25, 40.17, 40.13, 40.00,39.74, 38.72, 38.16, 38.04, 37.87, 37.61, 34.89, 34.63, 34.55, 32.27,31.76, 31.47, 29.10, 28.41, 28.03, 27.25, 26.77, 26.65, 26.43, 26.41,26.34, 25.88, 25.82, 25.69, 22.73, 22.46, 22.41, 17.68, 16.05, 16.02,15.93 ppm.

Example 2

This example describes method for making farnesane dimers from farnesenedimers.

A mixture of farnesene dimers (100 g, 0.245 mol) was placed in a 1 Lglass lined Hastaloy Parr hydrogenation vessel containing 0.75 g of 5%Pd/C. Hexane (300 mL) was added and the reactor assembled. The mixturewas placed under vacuum for one hour. The stirrer was started (400 rpm)and the reactor was pressurized to 600 psig with hydrogen. The mixturewas heated to 72° C. and the pressure allowed to drop to 300 psig atwhich time hydrogen was added to bring the pressure back to 600 psig.This process was repeated until hydrogen consumption had ceased. Thereactor was allowed to cool to 30° C. and the contents were filtered toremove the catalyst. Removal of the solvent under reduced pressureafforded 100 g (96.9%) of farnesane dimers consisting of 15 isomericcompounds of molecular weight 420 (GC/MS). Celite on a 60 mL mediumporosity sintered glass funnel to afford 200 g (98.3%) of clearcolorless oil. The presence of compounds II-A, II-C, II-B, and II-D wereconfirmed by ¹H NMR.

¹H (400 MHz, CDCl₃) d (multiplicity, coupling constant{s}, integration*)1.79-1.55 (m, 4.08H), 1.52 (m, J=6.8 Hz, 4.94H), 1.59-1.00 (m, 53.95H),1.05, 0.87, 0.86, 0.85, 0.85, 0.83, 0.83, 0.82, 0.81, 0.80, 0.79 (s,36.01 total H).

Farnesane 1,4-Dimer (90% pure): ¹H (400 MHz, CDCl₃) d (multiplicity,coupling constant{s}, integration*) 5.42 (m, 1H), 5.12 (m, 4H), 4.75 (m,2H), 2.10 (m, 15H), 1.98 (m, 8H), 1.682 (s, 3H), 1.680 (s, 3H), 1.60 (s,12H) ppm. * Integration values are relative areas peak to peak and notabsolute numbers of protons.

Example 3 Preparation of Dehydrosqualene from Farnesene

Farnesene (331.94 g, 1.627 mol) was stirred in 1025 mL 2-propanol andtriphenylphosphine (9.55 g, 36.4 mmol) was added followed by Palladium(II) acetylacetonate (3.91 g, 13.0 mmol). The mixture was heated at 85°C. for 7 hours and then allowed to cool to 25° C. After stirring 17hours, most of the 2-propanol was removed by rotary evaporation and theblack residue was suspended in one liter of 5% ethyl acetate in hexanes.The suspension was filtered through a silica gel pad 3 inches indiameter×3 inches high and the silica gel was washed with 500 mL 5%ethyl acetate in hexanes. The combined organic solutions wereconcentrated by rotary evaporation to give 328.3 g light yellow oil.

Alternative catalysts for this reaction include the combination of[Palladium (II) nitrate, sodium (2-methoxyphenoxide) or sodium phenoxideand triphenylphosphine] (see e.g., BCS Japan, v. 51(4), p. 1156-62(1978) and U.S. Pat. No. 3,859,374) as well as the combination of[bis(cyclooctadiene)nickel and tributylphosphine] (U.S. Pat. No.3,794,692). In certain embodiments, polymer bound triphenylphosphine canbe used in place of soluble triphenylphosphine. Other catalysts thatwere tried but which gave no useful conversion (<5%) include 5% Pd/C, 5%Pd/alumina, 5% Ru/C, palladium acetate, copper (II) acetylacetonate,cobalt (II) acetylacetonate, nickel (II) acetylacetonate, palladium (II)acetylacetonate (with no phosphine ligand), palladiumchloride+triphenylphosphine and palladium (0)dibenzylideneacetone+triphenylphosphine.

Example 4 Preparation of Squalane from Dehydrosqualene

Dehydrosqualene prepared above was placed in a one liter Parr pressurereactor and 1.1 g of 5% Pd/C was added. The vessel was sealed andevacuated under house vacuum for twenty minutes (ca. 20 torr) and thenpressurized with hydrogen gas up to 950 psi. The reaction is initiallyexothermic. After the initial exothermic stage of the reaction wascomplete the reaction temperature was maintained at 40° C. by externalheating and later at 60° C. Hydrogen gas was added as needed to maintainthe reaction rate. After 47 hours the reaction was judged complete byGCMS analysis so the crude reaction product was filtered through asilica gel pad 3 inches in diameter×3 inches high and the silica gel waswashed with 550 mL 5% ethyl acetate in hexanes. After removal of thesolvent by rotary evaporation the crude squalane weighed 332.6 g. Theproduct was distilled in 3 batches using a Kugelrohr bulb to bulbapparatus to give 282.4 g squalane (83.4% yield over both steps).

Example 5

This example provides lubricant properties for the farnasane dimersprepared according to Example 2 and squalane prepared according toExample 4.

TABLE 2 Thermal ASTM Farnasane Method Squalane Dimer Viscosity at 40°C., cst D 445 19.23 35.44 Viscosity at 100° C., cst D 445 4.14 5.71Kinematic Viscosity, cSt, - 40° C. D 445 6109.19 39410.14 Viscosityindex D 2270 118-132 100 Pour Point, ° C. D 97 <−60 C. −57 Flash Point,COC, ° C. D 92 232 234 Evaporative Loss, NOACK, wt. % D 5800 13.2 9.1Acid Number (mg KOH/g) D 974 0.056 1.25

Depending on the reaction conditions for making the farnesene/farnesanedimers (according to Examples 1 and 2), some amounts of higher oligomersmay be also present in the final compositions. The farnesane dimerstested in this example were distilled to remove any higher oligomersthat may be present.

In addition, thermal farnesene dimers have a viscosity at 40° C. of 17cSt and a viscosity at 100° C. of 5.03 cSt. The viscosity index of thethermal farnesene dimers was found to be 255.

Example 6

This example provides lubricant properties for various blends offarnasane dimers (II-A, II-B, II-C and II-D) and squalane. This exampleprovides lubricant properties for the farnasane dimers preparedaccording to Example 2 and squalane prepared according to Example 4. Thefarnesane dimers tested in this example were distilled to remove anyhigher oligomers that may be present.

TABLE 3 % Farnesane % dimers Squalane d₄₀ d₁₀₀ cP₄₀ cSt₄₀ cP₁₀₀ cSt₁₀₀VI 0 100 0.800 0.764 14.9 18.6 3.20 4.18 132 20 80 0.801 0.763 17.2 21.63.48 4.54 127 20 80 0.801 0.763 17.4 21.8 3.48 4.54 125 40 60 0.7970.767 19.3 24.1 4.56 5.76 115 80 20 0.831 0.763 25.4 30.6 4.23 5.54 119100 0 0.825 0.792 30.1 36.5 3.60 5.71 103 dx is the density attemperature x. cPx is the dynamic (absolute) viscosity at temperature x(in centipoises). cStx is the kinetic viscosity at temperature x (incentistokes).

In certain embodiment, a composition provided herein may comprise blendsfarnasane dimers (II-A, II-B, II-C and II-D) and squalene as describedin Table 4:

TABLE 4 % Farnesane dimers % Squalene 0 100 20 80 20 80 40 60 80 20 1000

In certain embodiment, a composition provided herein may comprise blendsfarnasane dimers (II-A, II-B, II-C and II-D) and dehydrosqualene asdescribed in Table 5:

TABLE 5 % Farnesane % dimers dehydrosqualene 0 100 20 80 20 80 40 60 8020 100 0

Example 7

This example provides lubricant properties for various blends offarnasene dimers (I-A, I-B, I-C and I-D) and squalane. This exampleprovides lubricant properties for the farnasene dimers preparedaccording to Example 2 and squalane prepared according to Example 4. Thefarnesene dimers tested in this example were distilled to remove anyhigher oligomers that may be present.

TABLE 6 % Farnesene dimers % Squalane cSt₄₀ cSt₁₀₀ VI 20 80 18.0 4.59185 50 50 17.2 4.58 200 80 20 17.0 4.56 202

Since modifications will be apparent to those of skill in the art, it isintended that the claimed subject matter be limited only by the scope ofthe appended claims.

What is claimed is:
 1. A compound selected from the group consisting of


2. An engine oil comprising the compound of claim
 1. 3. A transmissionfluid comprising the compound of claim
 1. 4. A hydraulic fluidcomprising the compound of claim
 1. 5. A gear oil comprising thecompound of claim
 1. 6. An industrial oil comprising the compound ofclaim
 1. 7. A metal-working fluid comprising the compound of claim
 1. 8.A process oil comprising the compound of claim
 1. 9. A marine oilcomprising the compound of claim
 1. 10. A grease comprising the compoundof claim
 1. 11. A lubricity enhancer comprising a compound selectedfrom:


12. A pour point depressant additive comprising a compound selected from


13. A fuel additive comprising a compound selected from


14. A composition comprising compounds:


15. The composition of claim 14 further comprising:


16. The composition of claim 14 further comprising squalane.
 17. Acomposition comprising:


18. The composition of claim 17 further comprising:


19. The composition of claim 18 further comprising squalane.